1. Field of the Invention
This invention relates to new organophosphoric acid ester anhydride derivatives and, more particularly, to new thiopyrophosphoric acid P,P,P'-trialkylester-P'-dialkylamide having a high insecticidal activity, high miticidal activity and high nematocidal activity in combination. This invention also relates to a process for the production of these new organophosphoric acid ester anhydride derivatives, as well as to an insecticidal, miticidal and nematocidal composition containing the above-mentioned new compound as active ingredient.
2. Description of the Prior Art
Many kinds of the organo-phosphorus compounds having the insecticidal activity, miticidal activity and/or nematocidal activity are known. For instance, thiopyrophosphoric acid P,P,P'-triethylester-P'-dimethylamide of the formula ##STR2## thiopyrophosphoric acid P,P,P'-triethylester-P'-diethylamide of the formula ##STR3## and dithipyrophosphoric acid P,P,P'-triethylester-P'-dimethylamide of the formula ##STR4## are known to have the insecticidal activity, as described in the "Izvestiia Akademii Nauk SSSR" pp. 1038-1041 (1954) and the "Khim i Primerenie" pp. 164-175 (1955). Furthermore, pyrophosphoric acid P,P,P'-triethylester-P'-dimethylamide is known to have the insecticidal activity, as described in the "Chemical Abstracts" Vol. 61 (1964) 8832 g and in the "Aspirantsk Roboty Nauchn" pp. 66-69 (1963). In Japanese patent application unexamined prepublication "Kokai" Sho 47-9600 (corresponding to German DT-OS 2054189), there is described that an organo-phosphorus compound of the formula ##STR5## wherein R.sup.1, R.sup.2 and R.sup.3 may be the same or different from each other and each are an alkyl group of 1-6 carbon atoms and R is a hydrogen atom, an alkyl group containing up to 6 carbon atoms or phenyl group which may be substituted with a halogen, nitro group and/or alkyl group exhibits an insecticidal activity. Besides, Japanes patent application unexamined prepublication "Kokai" Sho 53-59627 (corresponding to U.S. Pat. No. 4,110,440) discloses that an organophosphoric acid ester anhydride derivative of the general formula ##STR6## wherein R.sup.1 is a lower alkyl group of 1-6 carbon atoms and R.sup.2 is an alkoxyl group, alkylthio group, alkylamino group or dialkylamino group exhibits insecticidal, miticidal and nematocidal activities.
Amongst the insect pests, rice stem borer, brown planthoppers, rice leafhoppers, common cutworms and aphids may be mentioned as the main insect pests which are predominantely infesting aquatic rice plants cultivated in the submerged field or the crops cultivated in upland fields in recent years. For the purpose of combating these main insect pests, there have been applied large quantities of insecticides of the organo-phosphorus compound type, insecticides of the carbamate compound type, insecticides of the chlorinated compound type and others since a long time ago. In these years, there occurs an objectionable phenomena that the main insect pets have gained a resistance against the known insecticidal compounds which have extensively been used in the crop fields.